The idea for Local Legend Charters began when I was a young boy and would go out on charters with my father Kenneth Klein, Jr. Both he and my grandfather Kenneth Klein, Sr. were Olympic sailors, and have been an inspiration to me. After growing up on the water in the day charter industry, studying business on the mainland, and working as a Captain for four years, I decided it was time to start my own business. The name “Local Legends” pays homage to my family members who taught me about life, boating and the ocean. It also honors the rich history of our islands and the many people, past and present, who have left their mark on the Virgin Islands in a legendary fashion.
-Chris Klein


Our captains are expertly trained, and U.S. Coast Guard certified to ensure your safety. Our captains grew up in the Virgin Islands and have intimate knowledge of the islands and its waters. They are also skilled kite boarders, surfers and all-around watermen who are eager to share their passion for water sports and the Virgin Islands with you.


Chris Klein

Christopher Kenneth Klein, owner and founder of Local Legend Charters was born in Tortola and raised on St. Thomas and St. John until the age of seven. He grew up living and working on boats, trained by his father, a lifelong captain. Chris is an avid kite sailor, a gifted surfer and an all-around water man. He spent his summers in the Virgin Islands while living in Connecticut and while studying business at Northeastern University in Boston. In 2005, Chris moved back home to the Virgin Islands. With his prestigious U.S. Coast Guard Masters 50-ton license, he looks forward to showing you the best day of your vacation.



Our boats are designed for safety and comfort. Their unique hull design is ideal for our local waters and built to keep passengers dry and comfortable. Our spacious boats can accommodate up to 12 passengers each with comfortable seating and lots of storage for personal items, water toys and gear. We meticulously maintain our boats for safety and cleanliness.



We want your trip with Local Legends to be the highlight of your vacation. From planning your day to guiding you on your adventures, providing great customer service is our priority. Our customers will tell you that our professional and friendly team deliver a legendary experience time and time again.